β-Oxo Amides: Inexpensive and Efficient Ligands for the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction

Jin-Heng Li; Yue-Hua Zhang; Ren-Jie Song; Ye-Xiang Xie; Chen-Liang Deng; Yun Liang

doi:10.1055/s-2007-983891

PAPER

β-Oxo Amides: Inexpensive and Efficient Ligands for the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction

Jin-Heng Li*, Yue-Hua Zhang, Ren-Jie Song, Ye-Xiang Xie, Chen-Liang Deng, Yun Liang
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, P. R. of China
Fax: +86(731)8872531; e-Mail: jhli@hunnu.edu.cn;

Abstract

Alle Artikel dieser Rubrik

Abstract

β-Oxo amides were found to be inexpensive and efficient ligands for the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. In the presence of palladium(II) acetate and N-(4-methoxyphenyl)-3-oxobutanamide (L7), a variety of aryl halides, including deactivated aryl chlorides and heteroaryl halides, were successfully coupled to arylboronic acids in moderate to excellent yields providing very high turnover numbers (maximum TON <950,000 and TOF <79,167). It is noteworthy that the reaction is conducted under mild and aerobic conditions.

Key words

palladium(II) acetate - β-oxo amide - Suzuki-Miyaura cross-coupling reaction - aryl halides - arylboronic acids

Volltext

Referenzen

References

For reviews, see:

1a Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

1b Metal-Catalyzed Cross-Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; Weinheim: 1998.

1c Cross-Coupling Reactions, In Topics in Current Chemistry Vol. 219: Miyaura N. Springer; Berlin: 2002.

1d Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290

1e Hillier AC. Grasa GA. Viciu MS. Lee HM. Yang C. Nolan SP. J. Organomet. Chem. 2002, 653: 69

1f Metal-Catalyzed Cross-Coupling Reactions 2nd ed.: de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.

1g Bellina F. Carpita A. Rossi R. Synthesis 2004, 2419

1h Baudoin O. Eur. J. Org. Chem. 2005, 4223

1i Phan NTS. Van Der Sluys M. Jones CW. Adv. Synth. Catal. 2006, 348: 609

For selected representative papers on palladium/phosphine-catalyzed Suzuki-Miyaura cross-couplings, see:

2a Old DW. Wolfe JP. Buchwald SL. J. Am. Chem. Soc. 1998, 120: 9722

2b Wolfe JP. Buchwald SL. Angew. Chem. Int. Ed. 1999, 38: 2413

2c Wolfe JP. Singer RA. Yang BH. Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9550

2d Littke AF. Dai C. Fu GC. J. Am. Chem. Soc. 2000, 122: 4020

2e Netherton MR. Dai C. Neuschütz K. Fu GC. J. Am. Chem. Soc. 2001, 123: 10099

2f Liu S.-Y. Choi MJ. Fu GC. Chem. Commun. 2001, 2408

2g Revell JD. Ganesan A. Org. Lett. 2002, 4: 3071

2h Kirchhoff JH. Netherton MR. Hills ID. Fu GC. J. Am. Chem. Soc. 2002, 124: 13662

2i Tang Z.-Y. Lu Y. Hu Q.-S. Org. Lett. 2003, 5: 297

2j Hu Q.-S. Lu Y. Tang Z.-Y. Yu H.-B. J. Am. Chem. Soc. 2003, 125: 2856

2k Adjabeng G. Brenstrum T. Wilson J. Frampton C. Robertson A. Hillhouse J. McNulty J. Capretta A. Org. Lett. 2003, 5: 953

2l Jensen JF. Johannsen M. Org. Lett. 2003, 5: 3025

2m Walker SD. Barder TE. Martinelli JR. Buchwald SL. Angew. Chem. Int. Ed. 2004, 43: 1871

2n Barder TE. Walker SD. Martinelli JR. Buchwald SL. J. Am. Chem. Soc. 2005, 127: 4685

2o Guo M. Jian F. He R. Tetrahedron Lett. 2006, 47: 2033

For representative papers on palladium/carbene-catalyzed Suzuki-Miyaura cross-couplings, see:

3a Gstottmayr CWK. Bohm VPW. Herdtweck E. Grosche M. Herrmann W. Angew. Chem. Int. Ed. 2002, 41: 1363

3b Navarro O. Kelly RA. Nolan SP. J. Am. Chem. Soc. 2003, 125: 16194

3c Navarro O. Marion N. Oonishi Y. Kelly RA. Nolan SP. J. Org. Chem. 2006, 71: 685 ; and references cited therein

3d Marion N. Navarro O. Mei J. Stevens ED. Scott NM. Nolan SP. J. Am. Chem. Soc. 2006, 128: 4101

For representative papers on palladium/oxazoline-catalyzed Suzuki-Miyaura cross-couplings, see:

4a Tao B. Boykin DW. Tetrahedron Lett. 2002, 43: 4955

4b Gossage PA. Jenkins HA. Yadav PN. Tetrahedron Lett. 2004, 45: 7689

4c Wang L. Chin. J. Chem. 2006, 24: 770

4d Alcalde E. Dinares I. Mesquida N. Rodriguez S. Synthesis 2007, 865

4e Takemoto T. Iwasa S. Hamada H. Shibatomi K. Kameyama M. Motoyama Y. Nishiyama H. Tetrahedron Lett. 2007, 48: 3397

For representative papers on palladium/amine-catalyzed Suzuki-Miyaura cross-couplings, see:

5a Tao B. Boykin DW. Tetrahedron Lett. 2003, 44: 7993

5b Tao B. Boykin DW. J. Org. Chem. 2004, 69: 4330

5c Li J.-H. Liu W.-J. Org. Lett. 2004, 6: 2809

5d Li J.-H. Liu W.-J. Xie Y.-X. J. Org. Chem. 2005, 70: 5409

5e Li J.-H. Hu X.-C. Liang Y. Xie Y.-X. Tetrahedron 2006, 62: 31

5f Li J.-H. Zhu Q.-M. Xie Y.-X. Tetrahedron 2006, 62: 10888

5g Xie Y.-X. Li J.-H. Yin D.-L. Chin. J. Org. Chem. 2006, 26: 1155

6 For representative papers on palladium/amino acid-catalyzed Suzuki-Miyaura cross-couplings, see: Cui X. Tian Q. Wang J.-R. Liu L. Guo Q.-X. Synthesis 2007, 393

For representative papers on palladium/heterocycle-catalyzed Suzuki-Miyaura cross-couplings, see:

7a Mathews CJ. Smith PJ. Welton T. J. Mol. Catal. A: Chem. 2004, 214: 27

Pyridines:

7b Wu W.-Y. Chen S.-N. Tsai F.-Y. Tetrahedron Lett. 2006, 47: 9267

7c Mai W. Gao L. Synlett 2006, 2553

7d Jimenez-Sanchidrian C. Mora M. Ruiz JR. Catal. Commun. 2006, 7: 1025

Pyrazoles:

7e Mukherjee A. Sarkar A. Tetrahedron Lett. 2005, 46: 15

Imidazoles:

7f Grasa GA. Viciu MS. Huang J. Zhang C. Trudell ML. Nolan SP. Organometallics 2002, 21: 2866

7g Xiao J.-C. Shreeve JM. J. Org. Chem. 2005, 70: 3072

7h Hahn FE. Jahnke MC. Pape T. Organometallics 2007, 26: 150

Pyrimidines:

7i Li J.-H. Zhang X.-D. Xie Y.-X. Synlett 2005, 1897

8 For a representative paper on palladium/diazabutadiene-catalyzed Suzuki-Miyaura cross-couplings, see: Grasa GA. Hillier AC. Nolan SP. Org. Lett. 2001, 3: 1077

For representative papers on palladium/urea-catalyzed Suzuki-Miyaura cross-couplings, see:

9a Dai MJ. Liang B. Wang CH. You ZJ. Xiang J. Dong GB. Chen JH. Yang Z. Adv. Synth. Catal. 2004, 346: 1669

9b Chen W. Li R. Han B. Li B. Chen Y. Wu Y. Ding L. Yang D. Eur. J. Org. Chem. 2006, 1177

9c Cui X. Zhou Y. Wang N. Liu L. Guo Q.-X. Tetrahedron Lett. 2007, 48: 163

10 For representative papers on palladium/guanidine-catalyzed Suzuki-Miyaura cross-couplings, see: Li S. Lin Y. Cao J. Zhang S. J. Org. Chem. 2007, 72: 4067

For representative papers on palladium/hydrazone-catalyzed Suzuki-Miyaura cross-couplings, see:

11a Mino T. Shirae Y. Sakamoto M. Fujita T. Synlett 2003, 882

11b Mino T. Shirae Y. Sakamoto M. Fujita T. J. Org. Chem. 2005, 70: 2191

For representative papers on palladium/surfactant-catalyzed Suzuki-Miyaura cross-couplings, see:

12a Bhattacharya S. Srivastava A. Sengupta S. Tetrahedron Lett. 2005, 46: 3557

12b Liu L. Zhang Y. Wang Y. J. Org. Chem. 2005, 70: 6122

12c Xin B. Zhang Y. Cheng K. J. Org. Chem. 2006, 71: 5725

For selected representative papers on palladium/the other ligand-catalyzed Suzuki-Miyaura cross-couplings, see:

13a Chen M.-T. Huang C.-A. Chen C.-T. Eur. J. Inorg. Chem. 2006, 4642

13b Gupta AK. Song CH. Oh CH. Tetrahedron Lett. 2004, 45: 4113

13c Liu Q.-P. Chen Y.-C. Wu Y. Zhu J. Deng J.-G. Synlett 2006, 1503

13d Alonso DA. Botella L. Najéra C. Pacheco MC. Synthesis 2004, 1713

13e Alonso DA. . Pacheco MC. J. Org. Chem. 2002, 67: 5588

For selected representative papers on ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings see:

14a Deng Y. Gong L. Mi A. Liu H. Jiang Y. Synthesis 2003, 337

14b Bandgar BP. Bettigeri SV. Phopase J. Tetrahedron Lett. 2004, 45: 6959

14c Kantam ML. Roy S. Roy M. Sreedhar B. Choudary BM. Adv. Synth. Catal. 2005, 347: 2002

14d Liu W.-J. Xie Y.-X. Liang Y. Li J.-H. Synthesis 2006, 860

14e Deng C.-L. Guo S.-M. Xie Y.-X. Li J.-H. Eur. J. Org. Chem. 2007, 1457 ; and references cited therein

15a Buck E. Song ZJ. Tschan D. Dormer PG. Volante RP. Reider PJ. Org. Lett. 2002, 4: 1623

15b Shafir A. Buchwald SL. J. Am. Chem. Soc. 2006, 128: 8742

15c Altman RA. Buchwald SL. Org. Lett. 2007, 9: 643

15d Shafir A. Lichtor PA. Buchwald SL. J. Am. Chem. Soc. 2007, 129: 3490

15e Lv X. Bao W. J. Org. Chem. 2007, 72: 3863

According to the previous and present results, three roles of TBAB may play in the reaction: (i) activation of the active Pd(0) species with the formation of anionic species, (ii) stabilization of the low coordinate Pd(0) species, (iii) phase-transfer catalyst for the inorganic base/solvent/substrate/product phases. For representative papers on TBAB-improved Suzuki reactions, see:

16a Badone D. Baroni M. Cardamone R. Ielmini A. Guzzi U. J. Org. Chem. 1997, 62: 7170

16b Bedford RB. Blake ME. Butts CP. Holder D. Chem. Commun. 2003, 466

16c Lysén M. Köhler K. Synlett 2005, 1671 ; and references cited therein

16d Arvela RK. Leadbeater NE. Org. Lett. 2005, 7: 2101

16e Liu W.-J. Xie Y.-X. Liang Y. Li J.-H. Synthesis 2006, 860

17 Miyaura N. Yamada K. Suginome H. Suzuki A. J. Am. Chem. Soc. 1985, 107: 972

18 Venkatraman S. Li C.-J. Org. Lett. 1999, 1: 1133

19 Molander GA. Biolatto B. J. Org. Chem. 2003, 68: 4302

20 Wynberg H. van Driel H. J. Am. Chem. Soc. 1965, 87: 3998

21 Komatsu M. Ohgishi H. Ohshiro Y. Agawa T. Tetrahedron Lett. 1976, 17: 4589